Potassium Carbonate → HCID 82881970, Verbindung

HRID 1848728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848728
Cl[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[CH:17]=[C:18]([OH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]>C(#N)C>[F:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[O:25][CH2:2][C:3]1[CH:7]=[CH:6][N:5]([CH3:8])[N:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 4239233-(Chloromethyl)-1-methyl-1H-pyrazoleHCID 5209483-Fluoro-4-nitrophenol

Produkt 1

HCID 82881970HCID 82881970, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3-(chloromethyl)-1-methyl-1H-pyrazole (15.6 g, 0.12 mol) in acetonitrile (200 mL) was added K2CO3 (67 g, 0.48 mol) followed by 3-fluoro-4-nitrophenol (19 g, 0.12 mol). The mixture was stirred at 90° Celsius overnight. When the reaction was complete, it was cooled to RT and the solvent was concentrated to dryness. The resulting residue was dissolved in DCM (500 mL) and then washed with water (500 mL). The organic phase was separated, concentrated to dryness and purified by recrystallization from ethyl acetate (100 mL) to give the title compound. MS (ESI): mass calcd. for C11H10FN3O3, 251.07; m/z found, 252.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 8.05-7.99 (t, 1H), 7.33 (d, J=3, 1H), 6.86-6.84 (m, 1H), 6.81-6.78 (m, 1H), 6.29 (d, J=3, 1H), 5.11 (s, 2H), 3.88 (s, 3H).

Aufarbeitung

  1. temperatureit was cooled to RT
  2. concentrationthe solvent was concentrated to dryness
  3. dissolutionThe resulting residue was dissolved in DCM (500 mL)
  4. washwashed with water (500 mL)
  5. customThe organic phase was separated
  6. concentrationconcentrated to dryness
  7. custompurified by recrystallization from ethyl acetate (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-84607f07406448a7917f74b1798bf1fe
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952177B2

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